Lipase-Catalyzed Glucose Fatty Acid Ester Synthesis in Ionic Liquids

Ganske, Franka; Bornscheuer, Uwe T.

doi:10.1021/ol0511169

Cited by 143 publications

(80 citation statements)

References 22 publications

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“…Results showed that the maximum conversion (>49%) and enantiomeric excess (ee > 99.9%) of rac-CDPP were achieved after 6-h incubation at 30˝C in [Bmim] [PF 6 ]/hexane co-solvents system, where the tertiary structure of lipase was supposed to be well stabilized [82]. Ganske and Bornscheuer [83] 6 ] and pyridine (80:20, v/v) for acylation of 1-β-D-arabinofuranosyl-cytosine using CALB as a biocatalyst, and the results showed that the conversion was dramatically increased to 99.4% compared with other solvent systems.…”

Section: Biocatalysis In Mixture Solvents Of Organic Solvent and Ionimentioning

confidence: 99%

Enzyme Stability and Activity in Non-Aqueous Reaction Systems: A Mini Review

et al. 2016

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Abstract:Enormous interest in biocatalysis in non-aqueous phase has recently been triggered due to the merits of good enantioselectivity, reverse thermodynamic equilibrium, and no water-dependent side reactions. It has been demonstrated that enzyme has high activity and stability in non-aqueous media, and the variation of enzyme activity is attributed to its conformational modifications. This review comprehensively addresses the stability and activity of the intact enzymes in various non-aqueous systems, such as organic solvents, ionic liquids, sub-/super-critical fluids and their combined mixtures. It has been revealed that critical factors such as Log P, functional groups and the molecular structures of the solvents define the microenvironment surrounding the enzyme molecule and affect enzyme tertiary and secondary structure, influencing enzyme catalytic properties. Therefore, it is of high importance for biocatalysis in non-aqueous media to elucidate the links between the microenvironment surrounding enzyme surface and its stability and activity. In fact, a better understanding of the correlation between different non-aqueous environments and enzyme structure, stability and activity can contribute to identifying the most suitable reaction medium for a given biotransformation.

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Section: Biocatalysis In Mixture Solvents Of Organic Solvent and Ionimentioning

confidence: 99%

Enzyme Stability and Activity in Non-Aqueous Reaction Systems: A Mini Review

et al. 2016

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“…离子液体中产物比有机溶剂中的合成速率和产量更高, 主要原因是离子液体对脂肪酶的区域选择性有较大的影响 [44] . Ganske 等 [56] 发现脂肪酶 CrL 在有机溶剂四氢呋喃中催化葡萄糖 (21) 脂肪酶作为高效生物催化剂, 其催化活性与选择性跟脂肪酶的空间结构密切相关 [59] . 因此, 在研究离子液体对脂肪酶催化酯类合成过程的影响因素时, 需要对离子液体、pH、黏度、脂肪酶的空间结构及催化活性等诸多因素进行综合考虑.…”

Section: 影响脂肪酶的空间构象unclassified

Progress of Lipase-Catalyzed Ester Synthesis in Ionic Liquid

Li¹,

Wang²,

Leixia³

et al. 2012

Chin. J. Org. Chem.

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“…However, the poor miscibility of hydrophobic acyl donors and hydrophilic acceptors leads to a slow reaction rate. Different means have been developed to enhance miscibility of acyl donors and acceptors for lipase catalyzed reactions, including, polar organic solvents such as tert-butanol [12], ionic liquids [13], and ultrasound irradiation [14]. However, these methods suffer from some deficiencies, for instance, the usage of expensive equipment and solvents, downstream separation challenges and costs, environmental issues, and safety concerns.…”

Section: Introductionmentioning

confidence: 99%

Solvent-Free Lipase-Catalyzed Synthesis of Technical-Grade Sugar Esters and Evaluation of Their Physicochemical and Bioactive Properties

Hayes

Burton³

et al. 2016

Catalysts

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Technical-grade oleic acid esters of sucrose and fructose were prepared using solvent-free biocatalysis at 65˝C, without any downstream purification applied, and their physicochemical and bioactivity-related properties were evaluated and compared to a commercially available sucrose laurate emulsifier. To increase the conversion of sucrose and fructose oleate, prepared previously using solvent-free lipase-catalyzed esterification catalyzed by Rhizomucor miehei lipase (81% and 83% ester, respectively), the enzymatic reaction conditions was continued using CaSO 4 to control the reactor's air headspace and a lipase (from Candida antarctica B) with a hydrophobic immobilization matrix to provide an ultralow water activity, and high-pressure homogenation, to form metastable suspensions of 2.0-3.3 micron sized saccharide particles in liquid-phase reaction media. These measures led to increased ester content of 89% and 96% for reactions involving sucrose and fructose, respectively. The monoester content among the esters decreased from 90% to <70% due to differences in regioselectivity between the lipases. The resultant technical-grade sucrose and fructose lowered the surface tension to <30 mN/m, and possessed excellent emulsification capability and stability over 36 h using hexadecane and dodecane as oils, comparable to that of sucrose laurate and Tween ® 80). The technical-grade sugar esters, particularly fructose oleate, more effectively inhibited gram-positive foodborne pathogens (Lactobacillus plantarum, Pediococcus pentosaceus and Bacillus subtilis). Furthermore, all three sugar esters displayed antitumor activity, particularly the two sucrose esters. This study demonstrates the importance of controlling the biocatalysts' water activity to achieve high conversion, the impact of a lipase's regioselectivity in dictating product distribution, and the use of solvent-free biocatalysis to important biobased surfactants useful in foods, cosmetics, personal care products, and medicine.

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Lipase-Catalyzed Glucose Fatty Acid Ester Synthesis in Ionic Liquids

Cited by 143 publications

References 22 publications

Enzyme Stability and Activity in Non-Aqueous Reaction Systems: A Mini Review

Enzyme Stability and Activity in Non-Aqueous Reaction Systems: A Mini Review

Progress of Lipase-Catalyzed Ester Synthesis in Ionic Liquid

Solvent-Free Lipase-Catalyzed Synthesis of Technical-Grade Sugar Esters and Evaluation of Their Physicochemical and Bioactive Properties

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